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Volumn 62, Issue 27, 2006, Pages 6566-6573

C-S bond cleavage in the sensitized photooxygenation of tert-alkyl phenyl sulfides. The role of superoxide anion

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; BENZALDEHYDE; BENZOQUINONE; BORIC ACID; CATION; DIMER; ETHYLENE OXIDE DERIVATIVE; KETONE; MONOMER; NITROGEN; OXYGEN; SULFIDE; SUPEROXIDE;

EID: 33646900271     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.154     Document Type: Article
Times cited : (27)

References (42)
  • 32
    • 33646933663 scopus 로고    scopus 로고
    • note
    • 2.
  • 33
    • 33646937307 scopus 로고    scopus 로고
    • note
    • -1. We are very grateful to Dr. M. F. Gerini for performing this calculation.
  • 35
    • 33646913124 scopus 로고    scopus 로고
    • note
    • tert-Butyl cation is less stable and less selective than the cations from 1a and 1b, therefore it can also react with the solvent that is a weaker nucleophile than water.
  • 36
    • 33646915606 scopus 로고    scopus 로고
    • note
    • It might be suggested that the C-S bond breaking in the thiadioxirane is homolytic forming a benzenesulfonyl radical and a carbon radical. Reaction of the carbon radical with oxygen should lead to the observed reaction products. However, the formation of N-tert-butylacetamide is a clear indication that a carbocation is also formed and supports the heterolytic cleavage. Moreover, in this case the ketone would be the main reaction product, which is not observed.
  • 37
    • 33646926863 scopus 로고    scopus 로고
    • note
    • 17 However, those experiments were carried out at a significantly higher temperature, ≥40 °C.
  • 42
    • 0013634645 scopus 로고    scopus 로고
    • Scaiano J.C. (Ed), Academic, New York, NY
    • Bunce N.J. In: Scaiano J.C. (Ed). Handbook of Organic Photochemistry Vol. 1 (1999), Academic, New York, NY 243
    • (1999) Handbook of Organic Photochemistry , vol.1 , pp. 243
    • Bunce, N.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.